Crystal structure of diethyl 3,3'-{2,2'-(1E)-[1,4-phenyl-enebis(azan-1-yl-1-yl-idene)]bis-(methan-1-yl-1-yl-idene)bis-(1H-pyrrole-2,1-di-yl)}di-propano-ate.

The complete mol-ecule of the title compound, C26H30N4O4, is generated by crystallographic inversion symmetry. The dihedral angle between the planes of the benzene and pyrrole rings is 45.20 (11)°; the N atom bonded to the the benzene ring and the pyrrole N atom are in a syn conformation. The side chain adopts an extended conformation [N-C-C-C = 169.07 (17)° and C-O-C-C = -176.54 (17)°]. No directional inter-actions could be identified in the crystal packing.

Related literature

For the synthesis of di­pyrrole Schiff base ligands, see: Meghdadi et al.(2010 ▸); Munro et al. (2004 ▸). For the synthesis of pyrrole ester precursors, see: Koriatopoulou et al. (2008 ▸); Singh & Pal (2010 ▸). For the preparation of the title compound, see: Yang et al. (2004 ▸); Ourari et al. (2013 ▸).

Experimental

Crystal data

C26H30N4O4

M = 462.54

Monoclinic,

a = 21.6153 (10) Å

b = 8.1227 (4) Å

c = 13.9404 (8) Å

β = 94.395 (5)°

V = 2440.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 150 K

0.4 × 0.3 × 0.3 mm

Data collection

Agilent SuperNova (Single source at offset, Atlas) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013 ▸) T min = 0.613, T max = 1.000

6592 measured reflections

2900 independent reflections

1697 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.138

S = 1.10

2900 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrysAlis PRO (Agilent, 2013 ▸); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▸); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015005113/hb7371sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015005113/hb7371Isup2.hkl

Click here for additional data file.

. DOI: 10.1107/S2056989015005113/hb7371fig1.tif

A view of the mol­ecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.

CCDC reference: 1053761

Additional supporting information: crystallographic information; 3D view; checkCIF report

C26H30N4O4	F(000) = 984
Mr = 462.54	Dx = 1.259 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 21.6153 (10) Å	Cell parameters from 1750 reflections
b = 8.1227 (4) Å	θ = 3.8–27.5°
c = 13.9404 (8) Å	µ = 0.09 mm−1
β = 94.395 (5)°	T = 150 K
V = 2440.4 (2) Å3	Block, clear light colourless
Z = 4	0.4 × 0.3 × 0.3 mm

Agilent SuperNova (Single source at offset, Atlas) diffractometer	2900 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1697 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.063
Detector resolution: 10.3705 pixels mm-1	θmax = 29.5°, θmin = 2.9°
ω scans	h = −18→29
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −10→7
Tmin = 0.613, Tmax = 1.000	l = −19→18
6592 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055	H-atom parameters constrained
wR(F2) = 0.138	w = 1/[σ2(Fo2) + (0.0338P)2 + 0.0686P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
2900 reflections	Δρmax = 0.22 e Å−3
155 parameters	Δρmin = −0.26 e Å−3
0 restraints

Experimental. CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

	x	y	z	Uiso*/Ueq
O14	0.34059 (6)	0.02364 (17)	0.24674 (10)	0.0286 (4)
N1	0.45878 (7)	0.29578 (19)	0.01458 (12)	0.0225 (4)
O17	0.41066 (7)	0.2126 (2)	0.29870 (11)	0.0385 (4)
N7	0.34834 (7)	0.5212 (2)	0.01854 (13)	0.0231 (4)
C13	0.38269 (9)	0.1407 (2)	0.23355 (16)	0.0240 (5)
C6	0.37626 (9)	0.4878 (2)	−0.05699 (16)	0.0233 (5)
H6	0.3615	0.5387	−0.1140	0.028*
C5	0.42829 (9)	0.3787 (2)	−0.06151 (16)	0.0227 (5)
C8	0.29823 (9)	0.6351 (2)	0.00733 (15)	0.0213 (5)
C9	0.29548 (9)	0.7593 (2)	0.07499 (16)	0.0242 (5)
H9	0.3258	0.7654	0.1260	0.029*
C2	0.50726 (9)	0.2115 (3)	−0.01898 (17)	0.0285 (5)
H2	0.5353	0.1466	0.0181	0.034*
C11	0.44300 (9)	0.2904 (3)	0.11490 (15)	0.0248 (5)
H11A	0.4308	0.3996	0.1345	0.030*
H11B	0.4794	0.2581	0.1556	0.030*
C12	0.39047 (9)	0.1701 (3)	0.12900 (15)	0.0247 (5)
H12A	0.3521	0.2135	0.0983	0.030*
H12B	0.3991	0.0663	0.0983	0.030*
C15	0.33162 (10)	−0.0179 (3)	0.34693 (16)	0.0307 (6)
H15A	0.3205	0.0796	0.3820	0.037*
H15B	0.3694	−0.0636	0.3782	0.037*
C10	0.25193 (9)	0.6253 (2)	−0.06747 (16)	0.0244 (5)
H10	0.2528	0.5411	−0.1126	0.029*
C4	0.45880 (9)	0.3440 (3)	−0.14264 (17)	0.0283 (5)
H4	0.4484	0.3843	−0.2042	0.034*
C3	0.50810 (10)	0.2377 (3)	−0.11602 (17)	0.0318 (6)
H3	0.5361	0.1933	−0.1564	0.038*
C16	0.28000 (11)	−0.1429 (3)	0.34458 (18)	0.0412 (6)
H16A	0.2913	−0.2375	0.3085	0.062*
H16B	0.2427	−0.0953	0.3147	0.062*
H16C	0.2731	−0.1756	0.4091	0.062*

	U11	U22	U33	U12	U13	U23
O14	0.0361 (8)	0.0298 (9)	0.0205 (9)	−0.0087 (7)	0.0052 (7)	−0.0004 (7)
N1	0.0217 (9)	0.0226 (10)	0.0236 (10)	0.0014 (7)	0.0051 (8)	0.0034 (8)
O17	0.0397 (9)	0.0498 (11)	0.0266 (10)	−0.0165 (8)	0.0054 (8)	−0.0087 (8)
N7	0.0234 (9)	0.0209 (9)	0.0255 (10)	0.0023 (7)	0.0057 (8)	−0.0010 (8)
C13	0.0213 (11)	0.0228 (11)	0.0283 (13)	−0.0002 (9)	0.0032 (10)	−0.0042 (10)
C6	0.0258 (11)	0.0184 (11)	0.0260 (12)	−0.0029 (8)	0.0042 (10)	0.0040 (10)
C5	0.0241 (10)	0.0189 (11)	0.0257 (12)	0.0002 (8)	0.0064 (9)	0.0021 (10)
C8	0.0212 (10)	0.0192 (11)	0.0242 (12)	0.0008 (8)	0.0071 (9)	0.0028 (10)
C9	0.0209 (10)	0.0260 (12)	0.0255 (12)	−0.0006 (9)	0.0005 (9)	−0.0031 (10)
C2	0.0236 (11)	0.0255 (12)	0.0375 (14)	0.0074 (9)	0.0106 (10)	0.0027 (11)
C11	0.0236 (10)	0.0270 (12)	0.0239 (12)	0.0000 (9)	0.0019 (9)	0.0010 (10)
C12	0.0262 (11)	0.0254 (12)	0.0226 (12)	0.0010 (9)	0.0023 (9)	−0.0028 (10)
C15	0.0414 (13)	0.0290 (13)	0.0230 (13)	−0.0002 (10)	0.0102 (11)	0.0002 (11)
C10	0.0260 (11)	0.0219 (11)	0.0257 (13)	0.0001 (9)	0.0040 (10)	−0.0070 (10)
C4	0.0323 (12)	0.0261 (12)	0.0275 (13)	0.0012 (9)	0.0099 (10)	0.0063 (11)
C3	0.0330 (12)	0.0293 (13)	0.0351 (15)	0.0075 (10)	0.0153 (11)	0.0018 (11)
C16	0.0551 (16)	0.0357 (14)	0.0347 (15)	−0.0100 (11)	0.0152 (13)	0.0024 (12)

O14—C13	1.338 (2)	C2—C3	1.371 (3)
O14—C15	1.464 (2)	C11—H11A	0.9700
N1—C5	1.381 (3)	C11—H11B	0.9700
N1—C2	1.364 (2)	C11—C12	1.522 (3)
N1—C11	1.465 (3)	C12—H12A	0.9700
O17—C13	1.203 (2)	C12—H12B	0.9700
N7—C6	1.282 (2)	C15—H15A	0.9700
N7—C8	1.424 (2)	C15—H15B	0.9700
C13—C12	1.499 (3)	C15—C16	1.507 (3)
C6—H6	0.9300	C10—C9i	1.387 (3)
C6—C5	1.437 (3)	C10—H10	0.9300
C5—C4	1.381 (3)	C4—H4	0.9300
C8—C9	1.386 (3)	C4—C3	1.399 (3)
C8—C10	1.391 (3)	C3—H3	0.9300
C9—H9	0.9300	C16—H16A	0.9600
C9—C10i	1.387 (3)	C16—H16B	0.9600
C2—H2	0.9300	C16—H16C	0.9600
C13—O14—C15	115.83 (16)	C12—C11—H11B	109.2
C5—N1—C11	127.98 (16)	C13—C12—C11	111.61 (17)
C2—N1—C5	108.38 (18)	C13—C12—H12A	109.3
C2—N1—C11	123.62 (18)	C13—C12—H12B	109.3
C6—N7—C8	116.70 (18)	C11—C12—H12A	109.3
O14—C13—C12	112.02 (18)	C11—C12—H12B	109.3
O17—C13—O14	123.3 (2)	H12A—C12—H12B	108.0
O17—C13—C12	124.69 (18)	O14—C15—H15A	110.4
N7—C6—H6	117.1	O14—C15—H15B	110.4
N7—C6—C5	125.9 (2)	O14—C15—C16	106.64 (18)
C5—C6—H6	117.1	H15A—C15—H15B	108.6
N1—C5—C6	126.61 (19)	C16—C15—H15A	110.4
N1—C5—C4	107.45 (17)	C16—C15—H15B	110.4
C4—C5—C6	125.9 (2)	C8—C10—H10	119.9
C9—C8—N7	118.06 (19)	C9i—C10—C8	120.20 (18)
C9—C8—C10	119.07 (18)	C9i—C10—H10	119.9
C10—C8—N7	122.86 (18)	C5—C4—H4	126.0
C8—C9—H9	119.6	C5—C4—C3	108.1 (2)
C8—C9—C10i	120.71 (19)	C3—C4—H4	126.0
C10i—C9—H9	119.6	C2—C3—C4	106.86 (18)
N1—C2—H2	125.4	C2—C3—H3	126.6
N1—C2—C3	109.23 (19)	C4—C3—H3	126.6
C3—C2—H2	125.4	C15—C16—H16A	109.5
N1—C11—H11A	109.2	C15—C16—H16B	109.5
N1—C11—H11B	109.2	C15—C16—H16C	109.5
N1—C11—C12	111.88 (17)	H16A—C16—H16B	109.5
H11A—C11—H11B	107.9	H16A—C16—H16C	109.5
C12—C11—H11A	109.2	H16B—C16—H16C	109.5
O14—C13—C12—C11	−174.17 (16)	C5—N1—C11—C12	79.5 (2)
N1—C5—C4—C3	0.5 (2)	C5—C4—C3—C2	−0.8 (2)
N1—C2—C3—C4	0.9 (2)	C8—N7—C6—C5	179.01 (17)
N1—C11—C12—C13	169.07 (17)	C9—C8—C10—C9i	1.3 (3)
O17—C13—C12—C11	5.8 (3)	C2—N1—C5—C6	−177.15 (19)
N7—C6—C5—N1	−2.6 (3)	C2—N1—C5—C4	0.0 (2)
N7—C6—C5—C4	−179.3 (2)	C2—N1—C11—C12	−98.6 (2)
N7—C8—C9—C10i	179.47 (17)	C11—N1—C5—C6	4.5 (3)
N7—C8—C10—C9i	−179.52 (18)	C11—N1—C5—C4	−178.28 (18)
C13—O14—C15—C16	176.56 (17)	C11—N1—C2—C3	177.83 (18)
C6—N7—C8—C9	−134.2 (2)	C15—O14—C13—O17	−2.2 (3)
C6—N7—C8—C10	46.7 (3)	C15—O14—C13—C12	177.75 (16)
C6—C5—C4—C3	177.72 (19)	C10—C8—C9—C10i	−1.4 (3)
C5—N1—C2—C3	−0.6 (2)